Potassium Acetate → Methyl 4-(acetyloxy)-2-methyl-1-benzofuran-6-carboxylate

HRID 2233361노트

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HRID 2233361 반응식
[CH3:1][O:2][C:3](/[C:5](=[CH:10]/[C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1)/[CH2:6][C:7]([OH:9])=O)=[O:4].[C:17]([O-])(=[O:19])[CH3:18].[K+].O.C(OCC)(=O)C>C(OC(=O)C)(=O)C>[CH3:16][C:13]1[O:12][C:11]2[CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[C:7]([O:9][C:17](=[O:19])[CH3:18])[C:15]=2[CH:14]=1

참가 물질

5

반응물 3

HCID 517044Potassium AcetateHCID 22728543Water ethylacetateHCID 60145978HCID 60145978, 화합물

생성물 1

HCID 53249530Methyl 4-(acetyloxy)-2-methyl-1-benzofuran-6-carboxylate

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

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온도
140 °C

실험 절차

A mixture of E-3-methoxycarbonyl-4-(5-methylfur-2-yl)-but-3-enoic acid (Method 15; 1.39 g, 6.2 mmol) and potassium acetate (620 mg, 6.3 mmol) in acetic anhydride (12.5 ml) was heated at 140° C. for 15 mins. The reaction mixture was cooled and poured on to a water/ethyl acetate mixture; the aqueous layer was separated and the organic layer washed sequentially with saturated sodium bicarbonate solution and brine, dried (MgSO4) and evaporated in vacuo to yield the crude product as a dark crystalline mass. This was chromatographed (50 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%) to give the title compound as a pale yellow solid, 1.42 g (92%). NMR: 2.36 (s, 3H), 3.34 (s, 3H), 3.87 (s, 3H), 6.68 (s, 1H), 7.56 (s, 1H), 7.96 (s, 1H); m/z 247 (M−H)−, 97.1% by LC-MS.

후처리

  1. temperatureThe reaction mixture was cooled
  2. customthe aqueous layer was separated
  3. washthe organic layer washed sequentially with saturated sodium bicarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto yield the crude product as a dark crystalline mass
  7. customThis was chromatographed
  8. wash(50 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%)

출처 및 근거

ORD 기록
ord-6cca5735a1ac41599c822c4cb0f4dad8
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709505B2

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